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Flossmoor Station family recalls challenges of a quarter century in business

From left, Pam and George Armstrong and Dean and Carolyn Armstrong. The four spent time July 10 reminiscing about the 25 years Dean and Carolyn have owned Flossmoor Station Restaurant & Brewery. (Eric Crump/H-F Chronicle)

Starting a new business is a huge, time-consuming undertaking. 

Having a baby is a huge, time-consuming undertaking. 

Carolyn Armstrong did both — at the same time. 

While celebrating the 25th anniversary of Flossmoor Station Restaurant & Brewery owners Armstrong and her husband, Dean, sat with Dean’s brother, George, and his wife, Pam, and reminisced about the adventures along the way.


The first big adventure was opening the doors of the brewpub a month before their second daughter, Sarah, was due to arrive on the scene. The couple already had a 3-year-old, Ashley, on the team.

“I was bussing tables, washing dishes,” Carolyn said. “I had a playpen up in the office. They’d go to sleep up there. It was a lot.”

From left, DJ Phil Lee, Ashley Armstrong and Sarah
Armstrong spin tunes at the Flossmoor Station
25th anniversary celebration on July 10.
(Eric Crump/H-F Chronicle)

The couple said they bought the building, which at the time was a mini-mall filled with various shops, almost on a whim. They weren’t quite sure what they were going to do with it until they were on an antique-hunting trip to Michigan. 

They stopped for a bite to eat in a brew pub called Dusters. 

“The draft beer was the most awesome thing I’d ever had,” Dean said. 

That beer was the catalyst for Flossmoor Station.

There were many other adventures over the quarter century in business. 

The Armstrongs recalled the task of adding the caboose to the beer garden south of the building. For many years, the caboose served as an ice cream shop. It recently was converted into a small taproom.

“Getting the caboose was the easy part,” Carolyn said. And it turned out to be the cheapest part of the project.

The village required an engineering study, and the engineer recommened digging an 8-foot rock foundation to support the retired rail car. 

Two cranes were required to get the caboose from the adjacent tracks to its new home. Electric lines had to be taken down temporarily.   

On its trip to Flossmoor, the caboose was parked overnight in Gary, Indiana. 
“There was graffiti everywhere,” Carolyn said. So it had to be repainted. 

The investment has had benefits, though. It’s the centerpiece of what Dean says is the world’s best beer garden. His evidence for the claim?

“We’ve got a caboose. We’ve got a doggie park. We’ve got trains roaring by,” he said. 
The beer garden also has paid off during the pandemic.

While most restaurants were only able to do takeout service during significant periods of 2020, the Station was able to use outdoor seating to keep more of its business going.

Still, the pandemic was among the biggest challenges the Armstrongs faced, even compared with opening-while-pregnant.

“The last almost two years have been the hardest. I think I’ve worked harder than ever,” Carolyn said. 

Her example was not lost on her daughters, who grew up watching the restaurant and brewery evolve.

Ashley and Sarah were guest DJs at the anniversary celebration on July 10. They took a moment to talk about the experience. 

Sarah said when she was attending Parker Junior High she was a bit self-conscious about being the owners’ daughter, but as she got older she began to appreciate the central role the business played in the village.

Many of her peers worked alongside her, she said, becoming like a big family.

“It’s always been cool to see how my mom has provided a place for us to work,” she said. “I’ve always been so proud of my mom. This place has continued to grow and evolve. It’s really the center piece of coming home. Everyone can come and reconnect.”

Ashley said she and her sister have become entreprenuers themselves, following in their mother’s footsteps. They have a health and fitness social media presence as “Strong Sistas” and are in the process of developing a regenerative farm.

“I think the coolest thing … was seeing my mom pursue her dream every single day,” Ashley said. “Growing up with that environment was inspiring and motivating for us as little girls.”

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